Classifications

• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
  • C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon

Definitions

• This invention relates to liquid crystal compositions comprising compounds having a silacyclohexane ring, and liquid crystal display devices containing the same.
• Liquid crystal display devices are devices utilizing the optical anisotropy and dielectric anisotropy possessed by liquid crystal materials. According to the display mode, there are various types including the TN (twisted nematic), STN (super-twisted nematic), SBE (super-twisted birefringent effect), DS (dynamic scattering), guest-host, DAP (distortion of aligned phase) and OMI (optical mode interference) types.
• the most common display devices are ones having a twisted nematic structure on the basis of the Schutt-Hellfritt effect.
• liquid crystal materials used in these liquid crystal display elements more or less vary according to the display mode, a wide liquid crystal temperature range and stability to moisture, air, light, heat and electric fields are commonly required for all display modes. Moreover, it is desired that the liquid crystal materials have low viscosity and provide a short addressing time, a low threshold voltage and high contrast in the cells. At present, there is no single compound that meets all of these requirements, and it is a matter of fact that liquid crystal mixtures obtained by mixing several or several tens of liquid crystal compounds and/or latent liquid crystal compounds are being used. Accordingly, it is also important that these components are easily miscible with each other.
• the active matrix (AM)-driven twisted nematic (TN) mode using a thin film transistor (TFT) element array or thin film diode (TFD) element array is being extensively employed owing to its high image display quality (i.e., high fineness, high contrast and high response speed).
• TFT thin film transistor
• TFD thin film diode
• the simple matrix-driven STN mode has achieved an improvement in display quality owing to the development of new driving methods such as the multi-line selection method, and is finding its own applications.
• R d ⁇ ⁇ n in which d is the cell gap size and ⁇ n is the refractive index anisotropy of the liquid crystal material.
• a value of R in the range of 0.8-0.9 is chosen in the STN mode.
• the ⁇ n of the liquid crystal material be in the range of 0.08-0.09 for the first minimum of transmittance and in the range of 0.11-0.20 for the second minimum of transmittance and the STN mode.
• liquid crystal materials In the case of AM driving, it is required from reasons characteristic of this driving method that liquid crystal materials have what is called a signal voltage holding property.
• This signal voltage holding property designates the degree of drop of the signal voltage applied to picture elements containing a liquid crystal material, within a given frame period. Accordingly, when the signal voltage does not drop (i.e., when the voltage holding ratio is 100%), the alignment of the liquid crystal molecules is not broken and, therefore, no reduction in contrast is caused.
• this voltage holding property is affected by the environment in which the liquid crystal panel is used, so that the lifetime of the property tends to be shortened in an environment exposed to high-intensity light as in liquid crystal panels for projection use, and in an environment exposed to high temperatures as in liquid crystal panels for use on automobiles.
• the threshold voltage of a liquid crystal material can be lowered by increasing its dielectric constant anisotropy ( ⁇ ).
• liquid crystal materials having high ⁇ have the disadvantage that they fail to achieve a high voltage holding ratio.
• liquid crystal compositions having a high ⁇ n of 0.13 to 0.25, a low viscosity of 30 cP or less, a low threshold voltage and a high voltage holding ratio can be obtained by adding thereto, as a required component, a compound having both a silacyclohexane ring and a tolan structure of the formula or a mixture of a compound having the silacyclohexane ring and a compound having the tolan structure.
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising one or more compounds wherein at leapt one of the compounds contains a trans-1-sila-1,4-cyclohexylene, or trans-4-sila-1,4-cyclohexylene group, and at least one of the compounds is of the general formula (I) wherein
• the present invention provides a liquid crystal composition comprising one or more compounds of the general formula (I) and one or more compounds having a silacyclohexane ring.
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising one or more compounds of the general formula (Ia), (Id), or (Ig), and one or more of compounds of the general formula (Ib), (Ic), (Ie) or (If) wherein R, X, Y 1 , Y 2 , L 1 , n are as defined for the general formula (I).
• the present invention provides a liquid crystal composition comprising at least one compound of the above general formula (I) and at least one compound of the general formula (II) wherein
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising at least one compound of the above general formula (I) and at least one compound of the general formula (III), (IV) or (V) wherein
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising at least one compound of the above general formula (I), at least one compound of the above general formula (II), and at least one compound of the above general forumula (III), (IV), or (V).
• at least one compound of the liquid crystal composition has to have a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, although the compound does not have to be of the general formula (I), (II), (III), (IV), or (V).
• the present invention provides a liquid crystal composition comprising at least one compound of the general formula (I), and at least one compound of the general formula (VI), (VII) or (VIII) wherein
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising at least one compound of the above general formula (I), at least one compound of the above general formula (II), and at least one compound of the above formula (VI), (VII) or (VIII).
• at least one compound of the liquid crystal composition has to have a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, although the compound does not have to be of the general formula (I), (II), (VI), (VII), or (VIII).
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising at least one compound of the above general formula (I), at least one compound of the above general formula (II), at least one compound of the above general formula (III), (IV), or (V), and at least one compound of the above formula (VI), (VII) or (VIII).
• at least one compound of the liquid crystal composition has to have a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, although the compound does not have to be of the general formula (I), (II), (III), (IV), (V), (VI), (VII), or (VIII).
• the present invention provides a liquid crystal display elements containing these liquid crystal compositions.
• the present invention relates to liquid crystal compositions comprising one or more compounds having high ⁇ n of 0.13 or more and low viscosity of 30 cP or less and containing a conventionally unknown silacyclohexane ring in the molecular structure.
• These liquid crystal compositions can be used in the TN mode at the first and second minima and in the STN mode.
• these liquid crystal compositions have not only a low threshold voltage suitable for low-voltage driving and a high voltage holding ratio under severe conditions, but also a nematic liquid crystal phase over a wide temperature range, good mutual solubility of various liquid crystal compounds, and stability to moisture, air, light, heat and electric fields.
• the threshold voltage can be lowered without increasing ⁇ excessively, and a high voltage holding ratio can be achieved at the same time.
• liquid crystal compositions are useful in applications requiring high ⁇ n and low viscosity, such as low-temperature poly-TFT liquid crystal panels for car navigators.
• R represents any of the following groups:
• (O) s C p H q F r are as follows: CH 2 CH 2 F, CH 2 CHF 2 , CH 2 CF 3 , CH 2 CH 2 CF 3 , CF 2 CH(F)CF 3 , OCH 2 CH 2 F, OCH 2 CHF 2 , OCH 2 CF 3 , OCH 2 CH 2 CHF 2 , OCH 2 CH 2 CF 3 , OCH 2 CF 2 CHF 2 , OCH 2 CF 2 CF 3 , OCF 2 CH(F)CF 3 and OCF 2 CF 3 .
• Y 1 and Y 2 are each H or F, L 1 is F, and n is 0, 1 or 2.
• the steric configurations of the silacyclohexane ring and the cyclohexane ring are both in trans form.
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising one or more compounds wherein at least one of the compounds contains a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group and at least one of the compounds is the general formula (I). That is, the compound having a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group may or may not be the compound of the general formula (I). It is preferable to he the compound of the general formula (I).
• the present invention provides a liquid crystal composition comprising one or more compounds of the general formula (I) and one or more of compounds having a silacyclohexane ring.
• the present invention provides a liquid crystal composition, preferably comprising one or more tolan compounds having no silacyclohaxane ring such as a compound of the general formula (Ia), (Id) or (Ig), and one or more compounds having a silacyclohexane ring.
• the present invention provides a liquid crystal composition, preferably comprising one or more tolan compounds having no silacyclohexane ring of the general formula (I) such as a compound of the general formula (Ia), (Id), or (Ig), and one or more tolan compounds having a silacyclohexane ring of the general formula (I) such as a compound of the general formula (Ib), (Ic), (Ie) or (If).
• a compound of the general formula (Ib) or (Ie) is the most preferable of the compounds of the general formulae (Ib), (Ic), (Ie) and (If).
• R, X, Y 1 , Y 2 , L 1 and n are as defined for the general formula (I), and the steric configurations of the silacyclohexane ring and the cyclohexane ring are both in trans form.
• k is an arbitrary integer in the range of 1 to 5.
• the present invention provides a liquid crystal composition comprising at least one compound of the general formula (I), at least one compound of the general formula (II), and at least one compound having a silacyclohexane ring.
• the present invention provides a liquid crystal composition comprising at least one compound of the general formula (I), and at least one compound of the general formula (II).
• at least one compound of the liquid crystal composition has to have a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, although the compound does not have to be of the general formula (I) or (II). It is preferable that the compound is of the general formula (I) or (II).
• the present invention provides a liquid crystal composition, preferably comprising one or more compounds of the general formula (I), and one or more compounds having a silacyclohexane ring A of the general formula (II) such as a compound of the general formula (IIa), (IIb), (IId), or (IIe).
• the present invention provides a liquid crystal composition, preferably comprising one or more tolan compounds having no silacyclohexane ring of the general formula (I) such as a compound of the general formula (Ia), (Id), or (Ig), and one or more tolan compounds having a silacyclohexane ring of the general formula (I) such as a compound of the general formula (Ib), (Ic), (Ie), or (If), in addition to one or more compounds of the general formula (II).
• one or more tolan compounds having no silacyclohexane ring of the general formula (I) such as a compound of the general formula (Ia), (Id), or (Ig)
• one or more tolan compounds having a silacyclohexane ring of the general formula (I) such as a compound of the general formula (Ib), (Ic), (Ie), or (If), in addition to one or more compounds of the general formula (II).
• a compound of the general formula (Ib) or (Ie) is the most preferable of the compounds of the general formulae (Ib), (Ic), (Ie), and (If).
• R, X, Y 1 and Y 2 are as defined for the general formula (I), and the steric configurations of the silacyclohexane ring and the cyclohexane ring are both in trans form.
• the partial skeleton structure (PS-1) is the same as in the general formula (I).
• R, X, Y 1 and Y 2 are as defined for the general formula (I), and the steric configurations of the silacyclohexane ring and the cyclohexane ring are both in trans form.
• the partial skeleton structure (PS-1) is the same as in the general formula (I).
• R, X, Y 1 and Y 2 are as defined for the general formula (I), and the steric configurations of the silacyclohexane and the cyclohexane ring are both in trans form.
• the partial skeleton structure (PS-1) is the same as in the general formula (I).
• the present invention provides a liquid crystal composition comprising one or more compounds of the general formula (I), and one or more compounds having a silacyclohexane ring, and if neccessary, one or more compounds of the general formula (III), (IV), or (V).
• the present invention provides a liquid crystal composition comprising one or more compounds of the general formula (I), one or more compounds of the general formula (II), and one or more compounds having a silacyclohexane ring, and if necessary, one or more compounds of the general formula (III), (IV), or (V).
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising one or more compounds wherein at least one of the compound is of general formula (I), and wherein at least one of the compound contains trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, and the liquid crystal composition may have, if necessary, one or more compounds of the general formula (III), (IV), or (V).
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising at least one compound of the general formula (I) and at least one compound of the general formula (II), and if necessary, one or more compounds of the general formula (III), (IV), or (V).
• one of the compounds of the liquid crystal composition has to have a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, although the compound does not have to be of the general formula (I), (II), (III), (IV), or (V).
• the compound with a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group is the compound of the general formula (I), (II), (III), (IV), or (V).
• the compound of the general formula (III) is the most preferable of the compounds of the general formulae (III), (IV), and (V).
• R, L 1 and n are as defined for the general formula (I) and the steric configurations of the silacyclohexane ring and the cyclohexane ring are both in trans form.
• R' is as defined for R, L 2 is F, and m is 0, 1 or 2.
• R, X, Y 1 , Y 2 , L 1 and n are as defined for the general formula (I), and the steric configurations of the silacyclohexane ring and the cyclohexane ring are both in trans form.
• the partial skeleton structure (PS-2) is the same as in the general formula (II).
• R, X, Y 1 , Y 2 , L 1 and n are as defined for the general formula (I), and the steric configurations of the silacyclohexane ring and the cyclohexane ring are both in trans form.
• L 2 is F, and m is 0, 1 or 2.
• the partial skeleton structure (PS-1) is the game as in the general formula (I).
• the present invention provides a liquid crystal composition comprising one or more compounds of the general formula (I) and one or more compounds having a silacyclohexane ring, and if necessary, one or more compound of the general formula (VI), (VII), or (VIII).
• the present Invention provides a liquid crystal composition comprising one or more compounds of the general formula (I), one or more compounds of the general formula (II) and one or more compounds having a silacyclohexane ring, and if necessary, one or more compound of the general formula (VI), (VII), or (VIII).
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising one or more compounds wherein at least one of the compound is of general formula (I), and wherein at least one of the compound contains trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, and the liquid crystal composition may have, if necessary, one or more compounds of the general formula (VI), (VII), or (VIII).
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising at least one compound of the general formula (I) and at least one compound of the general formula (II), and if necessary, one or more compounds of the general formula (VI), (VII), or (VIII).
• one of the compounds of the liquid crystal composition have to have a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, although the compound does not have to be of the general formula (I), (II), (VI), (VII), or (VIII).
• the compound with a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group is the compound of the general formula (I), (II), (VI), (VII), or (VIII).
• the present invention provides a liquid crystal composition
• a liquid crystal composition comprising at least one compound of the general formula (I) and if necessary, one or more compounds of the general formula (II), (III), (IV), (V), (VI), (VII), or (VIII).
• one of the compounds of the liquid crystal composition have to have a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group, although the compound does not have to be of the general formula (I), (II), (III), (IV), (V), (VI), (VII), or (VIII).
• the compound with a trans-1-sila-1,4-cyclohexylene or trans-4-sila-1,4-cyclohexylene group is the compound of the general formula (I), (II), (III), (IV), (V), (VI), (VII), or (VIII).
• the compound of the general formula (VI) or (VII) is the most preferable of the compounds of the general formulas (VI), (VII), (VIII).
• the following ones are especially preferred because they can provide the liquid crystal composition with a nematic liquid crystal phase over a wide temperature range, a high response speed, a low threshold voltage, a high voltage holding ratio, and low-temperature nematic stability.
• R for the compounds of the general formulae (I)-(VIII) are as follows:
• Preferred examples of the ring structures are (Ia), (Ib), (Id), (Ie), (Ig), (IIa), (IIc), (IId), (IIf), (IIIa), (IIIc), (IIId), (IIIf), (IIIi), (IVa), (IVc), (IVd), (IVf), (IVi), (Va), (Vf), (VIa), (VId), (VIe), (VIh), (VIIa), (VIIc), (VIIf), (VIIg), (VIIi), (VIIl), (VIIIa), (VIIIc), (VIIId) and (VIIIf).
• More preferred examples of the partial skeleton structure (PS-1) are as follows: wherein k is an arbitrary integer in the range of 1 to 5.
• More preferred examples of the partial skeleton structure are as follows.
• k is an arbitrary integer in the range of 1 to 5.
• PS-3 More preferred examples of the partial skeleton structure (PS-3) are as follows:
• one or more tolan compounds of the general formula (I) are preferably contained in total in 10 to 100 mol% of a total composition, while the other compound or compounds such as the compounds of the general formulae (II)-(VIII) are contained in total in 0 to 90 mol%of the total composition.
• One or more compounds of the general formula (II), which are added if necessary, are preferably added in total in 0 to 400 mol% against a total amount of one or more compounds of the general formula (I).
• One or more compounds of the general formula (III), (IV), or (V), which are added if necessary, are preferably added in 0 to 150 mol% against a total amount of one or more compounds of the general formula (I).
• One or more compounds of the general formula (VI), (VII), or (VIII), which are added if necessary, are preferably added in 0 to 110 mol% against a total amount of one or more compounds of the general formula (I).
• composition contains one or more compounds of the general formula (II), (III), (IV), (V), (VI), (VII), or (VIII), together with one or more compounds of the general formula (I), a compound or compounds having silane are contained preferably in total in 30 mol% or more of a total composition.
• the refractive index anisotropy ( ⁇ n) is enhanced as the proportions of the compounds of the general formulae (I), (II), (VI), (VII) and (VIII) become higher. Among others, the compounds of the general formula (I) are markedly effective.
• the proportion of group A [comprising one or more compounds selected from the compounds of the general formulae (Ia), (IIIa-c) and (IVa-c)] is in the range of 0 to 40 mol % and preferably 2 to 20 mol %.
• the proportion of group B [comprising one or more compounds selected from the compounds of the general formulae (Ib-g), (IIa-f), (IIId-i) and (IVd-i) and (Va-f)] is in the range of 60 to 100 mole % and preferably 70 to 96 mol %.
• group C comprising one or more compounds selected from the compounds of the general formulae (VIa-h), (VIIa-l) and (VIIIa-f)] is added, the proportion thereof is preferably in the range of 2 to 15 mol %.
• ⁇ In order to mix these components, desired amounts of minor components may be dissolved in major components by the application of heat. Alternatively, this may be done by dissolving various components in an organic solvent such as hexane, methanol or chloroform, mixing the resulting solutions, and then evaporating the organic solvent.
• an organic solvent such as hexane, methanol or chloroform
• liquid crystal compositions of the present invention which can be prepared in the above-described manner, have a nematic liquid crystal phase over a wide temperature range extending from a lower limit of -20°C or below to an upper limit of 70-100°C. They do not produce a smectic phase or a crystalline phase even after long-term storage at -20°C.
• the liquid crystal compositions of the present invention can further contain polychromatic dyes, such as azo dyes and anthraquinone dyes, to form a colored guest-host system. More specifically, dye-containing liquid crystal compositions prepared by adding, for example, a dichromatic dyes to a liquid crystal compositions in accordance with the present invention can he used in the phase transition guest-host mode.
• Azo dyes and anthraquinone dyes are suitable for use as dichromatic dyes in the present invention.
• the dichromatic dyes which can be added to the liquid crystal compositions of the present invention include azo dyes of the general formula wherein R 1 and R 2 are each a substituted or unsubstituted alkyl group of 1 to 7 carbon atoms, or a dialkylamino group where each alkyl group is a substituted or unsubstituted alkyl group of 1 to 7 carbon atoms, the substituted alkyl group is an alkyl group substituted with a plurality of fluorine atoms or an alkyl group in which -CH 2 - groups not adjacent to each other are substituted with O, S, NH, SO 2 , OCO, Z 1 to Z 9 are each hydrogen, methyl, methoxy or halogen, Z 1 and Z 2 , Z 4 and Z 5 , or Z 7 and Z 8 may be joined together to form an aliphatic ring, an aromatic
• liquid crystal compositions of the present invention can contain other additives including, for example, chiral dopants for imparting a desired twisting direction and strength thereto.
• the liquid crystal compositions containing such additives may be used in liquid crystal display elements by sandwiching them between transparent substrates on which active elements (such as TFTs or TFDs) or simple matrix electrodes are formed.
• active elements such as TFTs or TFDs
• These display elements may have various undercoats, orientation-controlling overcoats, polarizing plates, filters, reflective layers and the like as required.
• these display elements may be constructed in various ways, for example, by forming them into multilayer cells, combining them with other display elements, using semiconductor substrates, or using light sources.
• Liquid crystal compositions in accordance with the present invention were prepared by weighing out predetermined amounts of various components, mixing them, and heating the resulting mixture until a solution in an isotropic state was obtained.
• composition of mixture described in these examples, all percentages are mole percentages.
• T NI 72.6°C
• ⁇ n 0.160
• ⁇ 19.7 cP
• T NI 95.0°C
• ⁇ n 0.198
• ⁇ 21.1 cP
• ⁇ 5.9
• VHR 99.2%.
• T NI 99.5°C
• ⁇ n 0.156
• ⁇ 27.3 cP
• ⁇ 7.7
• VHR 99.2%.
• T NI 75.5°C
• ⁇ n 0.166
• ⁇ 22.6 cP
• ⁇ 7.5
• VHR 99.0%.
• T NI 70.3°C
• ⁇ n 0.146
• ⁇ 24.0 cP
• ⁇ 6.3
• VHR 99.2%.

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• 1997
  • 1997-03-27 JP JP9075124A patent/JPH09324178A/ja active Pending
  • 1997-03-31 US US08/828,707 patent/US5866037A/en not_active Expired - Fee Related
  • 1997-04-01 KR KR1019970012044A patent/KR100242560B1/ko not_active IP Right Cessation
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